One Gay at a Time

Before I met Smiles, I was chatting with a guy on OKCupid. After cruising the site, trying to find anything remotely resembling a prospective man, I managed to find a guy who was both attractive and seemed to have a great personality — at least based on his profile. He looked like he led an active lifestyle and was smiling in all of his pictures, so I sent him a message.

Surprisingly, he messaged me back shortly thereafter asking me to email him some pictures (my profile only has my torso pic). However, he added, “And just to be upfront about intentions, I’m seeing someone currently, but I’m so down to make legit guy friends. I don’t do well with the fem/gay scene so I’m always eager to meet more guys like us :)”

I wasn’t exactly thrilled, but I was also looking for friends. At the least, maybe I could get a wingman out of him. I responded, “Of course you’re seeing someone… All the good ones are!!! I can use friends just as much as I can use lovers ;)”

He seemed like a very genuine, down-to-earth guy. I was pleasantly surprised by his response. “Awww! Well you’re very cute. Why are you single?” he asked. We exchanged numbers and planned a time to meet on Thursday night immediately following work. Ironically enough, it was a night I double booked.

When my day was winding down, I texted him to confirm, but, he had to cancel. He had an impromptu second interview for a job, so I couldn’t exactly hold it against him for the last minute cancellation. Instead, I called up Sexy Eyes to see if he could grab coffee and already had plans later to meet Smiles for the first time.

I tried to reschedule with my new prospective friend, but I got no response after that. I wasn’t sure what happened exactly, but enough time passed that I lost interest. Then, out of the blue, I received a message, “Hey man, I broke up with my boyfriend So I’ve been in a funk. Sorry for flaking on you – I’m not usually like that, but the breakup wasn’t exactly amicable. If you want to give me a second chance, I’ve evened out and am down to chill.”

If you’ve ever read my blog, you know I’m all about second chances. However, now the roles were flipped. I was dating Smiles for a few weeks at this point, so this time I was the one looking for just friendship. For some odd reason, I didn’t make it a point to lay that out for him ahead of time, as he had done before the first time we planned to meet.

Wednesday after work, we met at Shima in the East Village, his neighborhood, for sushi. He was already waiting at the restaurant when I arrived. I sat and we immediately jumped into conversation. It was great because there was no tension or awkwardness. We jumped right in like we were old college buddies. I learned a lot about him over dinner — How he just moved to the city, what he wanted to do, what he did for fun, his family… The conversation flowed constantly. We really hit it off.

When dinner ended, we stood outside chatting a bit before he invited me back to his place to smoke and watch Archer, a show we found we shared a common love for.

The whole reason I went on this date was because my friends all encouraged me to date other people. They explained it was healthy to date a few people at the same time until you find one you really like. Things had become a but of a roller-coaster with Smiles emotionally. It went against every fiber of my being, but I decided to follow their advice. However, when push came to shove, I turned it into a friend date and couldn’t make a move. It was getting late, so after a full episode, I decided it was time for me to head home. I wanted to leave before things got awkward.

He may have thought we were on a date, but I was dating Smiles. And, as much as my friends told me I needed to be dating other people as well, I couldn’t do it. I couldn’t lead my new friend on while I had a strong interest in Smiles.

He walked me to the elevator to say goodbye. I could tell he was expecting a kiss. And, I can’t lie. I wanted to kiss him. I had a really good time, but like I said, I couldn’t lead him on like that. I knew where my true interests lay. I gave him a hug and said goodbye. I could see the disappointment in the expression on his face as he walked back into his apartment. I felt awful.

I knew I couldn’t leave things as they ended. I wanted a friendship from him, so I wanted him to know he didn’t just get rejected by me. I decided to text him to explain on my walk home.

I told him how great he is and how much I enjoyed myself with him, but I explained how I’d been dating Smiles since the night he first cancelled on me. He responded by noting, “Guess that was my loss.” We discussed it further. I realized I was wrong in not telling him my intentions going in to the date, but I didn’t know my intentions until the date was closing. I thought I could date more than one guy at a time, but it’s just not how I operate — At least not when I’d been seeing the guy for a few weeks. I could tell he wasn’t thrilled with the situation, but I had a feeling time would fix it, and we could start a great friendship.